Journal ArticleDOI
Dimethylformamide as a carbon monoxide source in fast palladium-catalyzed aminocarbonylations of aryl bromides
TLDR
The carbonylation procedure reported herein, which relies on the in situ generation of carbon monoxide, serves as a convenient alternative to othercarbonylation methods and is particularly applicable to small-scale reactions where short reaction times are desired and the direct use of carbonmonoxide gas is impractical.Abstract:
Dimethylformamide (DMF) acts as an efficient source of carbon monoxide and dimethylamine in the palladium-catalyzed aminocarbonylation (Heck carbonylation) of p-tolyl bromide to provide the dimethylamide. Addition of amines to the reaction mixture in excess delivers the corresponding aryl amides in good yields. The amines employed, benzylamine, morpholine, and aniline, all constitute good reaction partners. The reaction proceeds smoothly with bromobenzene and more electron-rich aryl bromides, but electron-deficient aryl bromides fail to undergo aminocarbonylation. The reactions are conducted at 180-190 degrees C for 15-20 min with microwave heating in a reaction mixture containing imidazole and potassium tert-butoxide: the latter is required to promote decomposition of the DMF solvent at a suitable rate. The beneficial effects of controlled microwave irradiation as an energy source for the rapid heating of the carbonylation reaction mixture are demonstrated. The carbonylation procedure reported herein, which relies on the in situ generation of carbon monoxide, serves as a convenient alternative to other carbonylation methods and is particularly applicable to small-scale reactions where short reaction times are desired and the direct use of carbon monoxide gas is impractical.read more
Citations
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Journal ArticleDOI
Pd/C-catalyzed carbonylative C–H activation with DMF as the CO source
TL;DR: An interesting Pd/C-catalyzed carbonylative cyclization of N-arylpyridin-2-amine derivatives via C–H activation has been developed with DMF as the CO source, and the desired quinazolinones were formed in moderate to good yields with good functional group tolerance.
Journal ArticleDOI
Copper-Catalyzed Carbamoylation of Terminal Alkynes with Formamides via Cross-Dehydrogenative Coupling
TL;DR: KIE study indicates the cleavage of the carbamoyl C–H bond affording formamide radical is the rate-determining step.
Journal ArticleDOI
A Convenient and Efficient Palladium‐Catalyzed Carbonylative Sonogashira Transformation with Formic Acid as the CO Source
TL;DR: In this paper, a palladium-catalyzed carbonylative Sonogashira reaction of aryl iodides was developed with formic acid as the CO source and dicyclohexyl carbodiimide as the activator.
Journal ArticleDOI
A novel nickel-catalyzed synthesis of thioesters, esters and amides from aryl iodides in the presence of chromium hexacarbonyl
TL;DR: In this paper, a NiCl2 catalytic system under ligand-free conditions for the efficient thiocarbonylation, alkoxy carbonylation and amidocaronylation reactions of aryl iodides in the presence of Cr(CO)6 as the solid source of carbon monoxide under air was presented.
Journal ArticleDOI
The optimized microwave-assisted decomposition of formamides and its synthetic utility in the amination reactions of purines
TL;DR: In this paper, the microwave assisted decomposition of DMF was thoroughly studied and the reaction conditions (temperature, solvent effect, and effect of additives, such as acids, bases, and salts) were optimized for its use in amination reactions.
References
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Journal ArticleDOI
Progress in hydroformylation and carbonylation
TL;DR: The last 15 years of hydroformylation and carbonylation chemistry are reviewed in this article, including technical and commercial aspects, and the authors present a review of the most relevant papers.
Journal ArticleDOI
Developments in Microwave-Assisted Organic Chemistry
TL;DR: The CSIRO continuous microwave reactor (CMR) and microwave batch reactor (MBR) were developed for organic synthesis and operated at temperatures up to 200°C (1400 kPa) and 260°C(10 MPa) respectively as discussed by the authors.
Journal ArticleDOI
Microwave-assisted high-speed chemistry: a new technique in drug discovery.
Mats Larhed,Anders Hallberg +1 more
TL;DR: It is believed that the time saved by using focused microwaves is potentially important in traditional organic synthesis but could be of even greater importance in high-speed combinatorial and medicinal chemistry.
Journal ArticleDOI
Microwave-Promoted Palladium-Catalyzed Coupling Reactions
Mats Larhed,Anders Hallberg +1 more
Journal ArticleDOI
Fast Microwave-Assisted Preparation of Aryl and Vinyl Nitriles and the Corresponding Tetrazoles from Organo-halides
Mathias Alterman,Anders Hallberg +1 more
TL;DR: A very potent HIV-1 protease inhibitor (K(i) = 0.
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